The world is full of interesting people, the vast majority of whom don’t share nearly as often as I do. If I interview people, I give people a more natural way to share what they’ve learned in a way that other people can easily learn from. I also get to learn about things I can’t find on Google. Win all around.

I am better-suited to interviewing than many people are. I’m comfortable with the tech. I have a decent Internet connection. I have a flexible schedule, so I can adapt to guests. I use scheduling systems and can deal with timezones. I’ve got a workflow that involves posting show notes and even transcripts. I am reasonably good at asking questions and shutting up so that other people talk. I often stutter, but no one seems to mind. I usually take visual notes, which people appreciate. I’m part of communities that can get more value from the resources I share.

So, what’s getting in the way of doing way more interviews?

I feel somewhat self-conscious about questions and conversations. The Emacs Chats have settled into a comfortable rhythm, so I’m okay with those: introduction, history, nifty demo, configuration walkthrough, other tidbits. Frugal FIRE has a co-host who’s actively driving the content of the show, so I can pitch in with the occasional question and spend the rest of the time taking notes. It’s good for me to talk to other people out of the blue, but I don’t fully trust in my ability to be curious and ask interesting questions.

Hmm. What’s behind this self-consciousness? I think it could be that:

I don’t want to ask questions that have been thoroughly covered elsewhere. — But I know from my own blog that going over something again helps me understand it better, so I should worry less about repeating things. Judgment: IRRATIONAL, no big deal

I worry about awkward questions and making questions that are really more like statements. What are awkward questions? Closed-ended questions or ones that lead to conversational cul-de-sacs. — But the people I talk to also want to keep the conversation going, so between the two (or three) of us, we should be able to figure something out. And really, once we get going, it’s easy enough to ask more. So I’m anxious about being curious enough, but once we’re there, it’s easy. Judgment: IRRATIONAL, just get in there.

I worry about not being prepared enough, or being too forgetful. — But when did I ever claim to have an excellent memory or to be great at doing all the research? Maybe it’s enough to have the conviction that people have something interesting to share, and help them have the opportunity to share it. (And possibly warn interviewees about my sieve-of-a-brain in advance, so they’re not offended if I confuse them with someone else.) Judgment: IRRATIONAL

I’m not as used to the flow of an interview as I could be. It’s similar to but not quite the same as a regular conversation, which is something I’m not as used to as I should be. Oddly, it’s easier when I’m occupied with taking visual notes, because I can use my notes to remember interesting things to ask about (and the other person can watch it develop too). So maybe I should just always do that, and then the drawing is a super-neat bonus.

I hesitate to ask questions unless I have an idea of what I’m going to do with the answers. Why are the questions interesting? What do we want to explore? Who am I going to share this with, and why? I’ve gotten a lot of good feedback on Emacs Chats, so that makes it easy to keep going, but the one-offs can be harder to plan. Maybe I should just become more comfortable with asking in order to explore. Besides, I’m good at rationalization, so I can make sense of it during or after the conversation. And the kinds of interviews I do are also about letting people share what they think would be useful for other people, so I can follow their lead.

Really, what’s the point of being self-conscious when interviewing people? After all, I’m doing this so that the spotlight is on other people, and listeners can survive inexpertly-asked questions. Hey, if folks have the courage to get interviewed, that’s something. Like the way that it’s easier to focus on helping other people feel more comfortable at parties, I can try focusing on helping guests feel more comfortable during interviews.

And it’s pretty cool once we get into it. I end up learning about fascinating Emacs geekery, connecting with great people, and exploring interesting ideas along the way. Well worth my time, and people find the videos helpful.

So I think I can deal with some of those tangled emotions that were getting in the way of my interviews. (Look, I’m even getting the hang of calling them interviews instead of chats!)

What’s getting in the way of reaching out and inviting people on? I should be able to reach out easily and ask people to be, say, a guest for an Emacs Chat episode. I have good karma in the community, and there are lots of examples now of how such a conversation could go. How about Quantified Self? I’ve been thinking about virtual meetups or presentations for a while, since there are lots of people out there who aren’t close to a QS meetup. What’s stopping me?

I generally don’t think in terms of people when it comes to cool stuff or ideas: This makes it difficult for me to identify people behind clusters of interesting ideas, or recognize names when they come up in conversation. Still, it shouldn’t stop me from identifying one particular idea and then looking for the person or people behind that. If I discover other things about those people afterwards, that’s icing on the cake. Hmm… So maybe I should update my confederate map (time to Graphviz-ify it!), interview those people, and then branch out to a role model map. Oh! And I can apply Timothy Kenny’s idea of modeling people’s behaviours beforehand as a way to prepare for the interview, too. Judgment: CAN FIX

It would be easier to reach out if I’ve already written pre-psyched-up snippets I can add to my e-mail. Aha, maybe I should write myself an Org file with the reasons why this is a good thing and with snippets that I can copy and paste into e-mail. There are a lot of blog posts and podcast episodes on how to get better at requesting podcast interviews, and there are also resources for getting better at interviewing itself. I can change my process to include psyching myself up and sending a bunch of invitations. Judgment: CAN FIX

I’m slightly worried about pre-committing to a time – but really, Google+ events make it pretty easy to reschedule, and I haven’t needed to reschedule most things for my part. Judgment: IRRATIONAL.

All right. So, if I want to learn from people and share useful stuff, I can work on being more actively curious about people, and at inviting them to share what they know. I don’t have to ask brilliant New York Times-y questions. I just have to start from the assumption that they know something interesting, and give them an opportunity to share it with other people.

Why would people take the time to do interviews? Maybe they find themselves explaining things to people a lot, so a recording (plus visual notes! plus transcript!) can save them time and give them something to build more resources on. Maybe they’re looking for other people to bounce ideas off. Maybe it helps them understand things better themselves. I shouldn’t say no on their behalf. I can ask, and they can decide whether it makes sense for their schedule. Right. People are grown-ups.

Okay. What changes can I make?

Write an Org file psyching myself up with a condensed version of the reasoning above, and include snippets to copy and paste into e-mail invitations.

Trust that the future Sacha will sort out the questions and the flow of the conversation. And hey, even if it’s super awkward, you don’t get to “interesting” without passing through “meh” first. So just book it, and be super-nice to guests for helping out.

Hmm. That actually looks doable.

Have you gone through this kind of mental tweaking before? Any tips?

Thanks to Daniel Reeves and Bethany Soule for the nudge to write about this! Yes, I should totally pick their brain about Quantified Self, applied rationality, and other good things. Check out their blog at Messy Matters for awesome stuff. Oh, and Beeminder, of course. (Look, I’m even using Messy Matters as a nudge to play around with more colours and brushes! =) )

I’m interested in videocasting/podcasting as a richer and more interactive way to get stuff out of people’s heads and into other people’s heads. I’ve come to terms with the fact that most people don’t write anywhere near as much as I do, but that they know all sorts of things that they might not have realized yet. Talking to people seems to be a good way to help them share that, because many people find it easier to answer questions than to share on their own. Likewise, podcasts recorded live make it easier for me to bring in other people’s questions (bonus: I learn more in the process!). So, podcasting, even though actually talking to people is hard. Maybe if I do enough of it, I’ll get desensitized to the anxiety and I’ll get better.

Along those lines, I’ve been doing a weekly show for Google Helpouts providers. It’s a community of maybe a thousand people, which is a tiny niche in the Internet. I used to have co-hosts, but they’re on hiatus for various personal/business reasons. I did my first solo show the other week, and my second was last week. So far, I have managed to survive. I like it because Google Helpouts is a new platform and everyone’s still figuring things out. I’m fine with talking tech and maybe a little online marketing/customer service, but other people know so much more than I do about business and education, so interviews are a natural fit. I’m getting settled into a decent workflow involving Hangouts on Air, the Q&A module, MP3s, and even drawing sketchnotes while the conversation progresses.

Sketchnoting is oddly calming. I had done it from the very first show, when I had a co-host handle all the niceties of reaching out to people, introducing them on air, and asking questions. For a kick, I tried seeing if I could do it even when hosting solo, and it worked out fine. You’d think adding one more thing to do during the show would drive me crazy from multi-tasking, but actually, drawing keeps me not-stressed-out enough to listen well, ask follow-up questions (since I have my notes handy!), and help people follow along with the conversation or catch up afterwards. Besides, it’s a good excuse to swap out my webcam image for the screenshare, so I don’t have to be “on” all the time.

So the interview itself is fine, and it will get better as I pick up more experience.

Then there’s all the rest of the processes around that. I typically stay up about two hours after the end of the show. I chat with participants off-air for 30-45 minutes (this is usually the most fun segment!) and then handle all the post-work, since I like it when the resources are posted right away. That way, I don’t have to go back and work on it again. Although it’s certainly possible to just let the video be automatically posted on my YouTube channel and be done with it, I like putting together the video, my visual notes, an MP3 download (for the people who prefer to listen to the podcast while, say, doing chores or walking around), and eventually a transcript. If I’m going to do something, I might as well use it as an opportunity to explore what awesomeness look like. =)

That said, wouldn’t it be awesome to be able to document my processes so that I can do them without worrying about missing a step, and so that other people could take care of making things happen? I’d love to worry less about identifying, inviting, and coordinating potential guests, too. Someday.

Since many of the things I do involve my Google account, this probably means building trust carefully. I was thinking about what sequence of activities might make sense in terms of trust.

Come to think of it, I can improve my post-podcast process by parallelizing some of the tasks that take a long time to do. Maybe I’ll even figure out how to automate some of those tasks, like perhaps getting the ID3 information from a spreadsheet.

Here’s a list that’s roughly in order of trust:

Typing

If there are visual notes, type in the text of the images and send them to me.

Create transcripts suitable for copying and pasting into the blog posts.

Tech

Make sure the podcast shows up correctly in popular directories.

Add the text from 1 and 2 above to the blog posts for greater searchability.

Write the blog posts with the video, audio, images (if any), and additional resources; update the redirection in WordPress.

Create the announcement in WordPress.

Update the WordPress redirection information for the event.

Download the video from YouTube and extract the MP3; add metadata and upload it to archive.org

Draft or send invitations to possible show guests. Coordinate acceptance and schedule.

Do research on the scheduled guest. Compile a short report with their bio and possibly interesting questions to ask.

Research and suggest potential guests, including reasons why.

The biggest risk, I guess, is that someone goes rogue with my Google Account. Goodness knows enough people have had that kind of problem with people breaking into their accounts. Working with assistants I pick myself (since I work with people who have a good reputation) and making an effort to be an excellent client could lower that risk. I’ve also separated my domain administration account from my regular e-mail account. At some point, I’ll just have to trust (and verify).

Why wait until 2014 to start working on things that I think are a good idea? =) Since I’ve been listening to a lot of podcasts while commuting or walking around, I figured I should start making some as well so that people can learn more conveniently. Besides, it will be a great way to practise producing shows and sharing ideas. Here’s what I’ve been working on:

Helpers Help Out – a weekly show for Google Helpouts providers (~700 people, pretty exclusive at the moment =) )